US8642804B2 - Method of adsorbing and method of recovering fluorine-containing compound - Google Patents

Method of adsorbing and method of recovering fluorine-containing compound Download PDF

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US8642804B2
US8642804B2 US12/676,292 US67629208A US8642804B2 US 8642804 B2 US8642804 B2 US 8642804B2 US 67629208 A US67629208 A US 67629208A US 8642804 B2 US8642804 B2 US 8642804B2
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fluorine
containing compound
active carbon
adsorption
carbon
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US20100197964A1 (en
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Masaki Kuramitsu
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Daikin Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/34—Regenerating or reactivating
    • B01J20/3483—Regenerating or reactivating by thermal treatment not covered by groups B01J20/3441 - B01J20/3475, e.g. by heating or cooling
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C02F1/283—Treatment of water, waste water, or sewage by sorption using coal, charred products, or inorganic mixtures containing them
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/10—Inorganic compounds
    • C02F2101/12—Halogens or halogen-containing compounds
    • C02F2101/14—Fluorine or fluorine-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/34—Organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/36—Organic compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2303/00—Specific treatment goals
    • C02F2303/16—Regeneration of sorbents, filters

Definitions

  • the present invention relates to a method of adsorbing a C 2 -C 6 fluorine-containing compound, in which the C 2 -C 6 fluorine-containing compound contained in a liquid phase is capable of highly adsorbed, and a method of recovering the C 2 -C 6 fluorine-containing compound, in which the fluorine-containing compound is capable of highly recovered from an active carbon.
  • the present invention is capable of efficiently and selectively recovering the C 2 -C 6 fluorine-containing compound from a liquid phase, such as waste water from a plant, waste water from households and rivers.
  • a liquid phase such as waste water from a plant, waste water from households and rivers.
  • active carbon capable of recycling active carbon and recovering the adsorbed substances by desorbing the adsorbed substances from the active carbon which has adsorbed.
  • a C 2 -C 6 fluorine-containing compound for example, perfluorohexanoic acid (PFHA) has a solubility in water of about 20% at normal temperature, which is about 100 times of the solubility of perfluorooctanoic acid (PFOA) in water. Therefore, the adsorption rate of general active carbon, for example, general-purpose active carbon for waste water which was conventionally used is 5% or less at normal temperature and pH 7.
  • PFHA perfluorohexanoic acid
  • PFOA perfluorooctanoic acid
  • Patent Document 1 JP-A-09-315809
  • An object of the present invention is to provide a method of highly adsorbing a C 2 -C 6 fluorine-containing compound and a method of recovering the C 2 -C 6 fluorine-containing compound.
  • the present invention is based on the fact that the C 2 -C 6 fluorine-containing compound is highly adsorbed by an active carbon which has been subjected to a particular treatment.
  • the present invention provides a method of adsorbing a C 2 -C 6 fluorine-containing compound, wherein the C 2 -C 6 fluorine-containing compound is adsorbed by an active carbon by contacting a liquid containing the C 2 -C 6 fluorine-containing compound with the active carbon.
  • the method of adsorbing the C 2 -C 6 fluorine-containing compound may be used for a method of treating a liquid which contains the C 2 -C 6 fluorine-containing compound.
  • the present invention further provides a method of desorbing the C 2 -C 6 fluorine-containing compound, wherein the C 2 -C 6 fluorine-containing compound is desorbed from the active carbon by heating the active, which has adsorbed the fluorine-containing compound, to a temperature of 150° C. or more.
  • the present invention is capable to highly adsorb the C 2 -C 6 fluorine-containing compound.
  • it is capable to recycle the active carbon by heating the active carbon to a temperature of 150° C., which is suitable for desorption and avoids heat decomposition of the fluorine-containing compound. It is capable to recycle a C 2 -C 6 fluorine-containing surfactant by collecting and concentrating the desorbed matters.
  • FIG. 1 is a schematic view of an apparatus for desorbing active carbon, which is used in Example 3 of the present invention.
  • the active carbon is highly activated in order to improve the physical adsorptivity of the active carbon and the specific surface area of the active carbon is increased to 1500 m 2 /g or more.
  • the chemical adsorptivity of the active carbon is also improved by impregnating the surface of the active carbon with an ion.
  • the adsorption rate of the active carbon can be improved to 10% or more, for example 20% or more.
  • the adsorption rate (%) is given by: [[(Concentration of fluorine-containing compound in initial raw water [ppm]) ⁇ (Concentration of fluorine-containing compound in treated water after adsorption [ppm])] ⁇ (Amount of raw water [g])]/[(Amount of used active carbon [g]) ⁇ 1000,000] ⁇ 100[%].
  • the active carbon to be used for the present invention can be produced from carbonaceous materials.
  • a material which produces an active carbon by carbonization or activation can be used.
  • Such material includes, for example, materials of plant origin such as woods, sawn wood, charcoal, coconut shell, fruit shell such as walnut shell and seeds of fruits; materials of mineral origin, for example, coal such as peat, lignite, brown coal, bituminous coal and anthracite coal, pitch such as petroleum pitch and coal pitch, cokes, tar such as coal tar and petroleum tar, petroleum distillates residues; natural materials, for example, cellulosic fiber such as cotton and rayon, and synthetic materials such as phenolic resin, polyvinyl alcohol and polyacrylonitrile.
  • the form of the active carbon and the carbonaceous material includes powder form, granular form, fibrous form and any form which is prepared by molding the material.
  • An active carbon can be produced from the carbonaceous material by subjecting the carbonaceous material to a treatment such as carbonization or activation.
  • the carbonization may be performed by, for example, heat retorting the carbonaceous material at a temperature between about 300 and 700° C.
  • the activation may be performed by, for example, medicament activation using, for example, zinc chloride, phosphoric acid, sulfuric acid, calcium chloride, sodium hydroxide or potassium hydroxide, gas activation using, for example, steam, carbon dioxide, oxygen gas, combustion exhaust gas or a mixture gas thereof.
  • the size of the active carbon is generally in a range between 0.5 and 5.0 mm. Specific surface area of the active carbon can be increased by an activation.
  • the active carbon preferably has a specific surface area of at least 1,500 m 2 /g, for example from 1,500 to 2,500 m 2 /g and particularly from 1,800 to 2,500 m 2 /g.
  • the active carbon preferably has a specific surface area of at least 2000 m 2 /g.
  • the active carbon has an improved adsorption performance by subjecting it to a steam activation treatment.
  • the active carbon is exposed to a steam at a temperature of at least 120° C., for example from 130 to 350° C., particularly from 150 to 1000° C. and at a pressure of at least 0.2 MPa, for example from 0.5 to 15 MPa and particularly from 1 to 15 MPa.
  • the treatment time of the steam activation may be generally from 10 seconds to 50 hours, for example, from 10 minutes to 10 hours.
  • the active carbon may be heated in a furnace.
  • the surface of the active carbon may be impregnated with a cation.
  • the cation include a metal ion, a metal oxide ion and an ammonium ion.
  • the metal include a metal atom selected from Groups 1 to 13 of the Periodic Table of the Elements, for example, an alkaline metal (for example, Li, Na and K), an alkaline earth metal (for example, Mg and Ca), and Ti, Zr, V, Cr, Fe, Ni, Cu and Zn.
  • the C 2 -C 6 fluorine-containing compound (that is, the fluorine-containing compound having 2 to 6 carbon atoms) is selected from carboxylic acids, particularly aliphatic carboxylic acids having an aliphatic group (particularly an alkyl group) which is partially or fully substituted with fluorine atoms.
  • the fluorine-containing compound is preferably a compound which is represented by the general formula (1) or a salt thereof: C x F y COOH (1) wherein x is an integer from 1 to 5 and y is an integer from 3 to 11.
  • the salt of the fluorine-containing compound include a metal salt, an ammonium salt and an amine salt.
  • the metal salt include a salt of an alkaline metal, for example, lithium, sodium and potassium, or a salt of an alkaline earth metal, for example, calcium and magnesium.
  • fluorine-containing compound examples include perfluorohexanoic acid (PFHA), perfluorobutanoic acid (PFBA).
  • PFHA perfluorohexanoic acid
  • PFBA perfluorobutanoic acid
  • salts of the fluorine-containing compound include ammonium perfluorohexanoate salt (APFH).
  • the fluorine-containing compound generally has a function as a surface active agent.
  • adsorption and desorption of the fluorine-containing compound can be performed with using an active carbon.
  • the fluorine-containing compound can be recovered by desorbing the adsorbed substances such as the fluorine-containing compound from the active carbon.
  • the concentration of the fluorine-containing compound in the liquid containing the fluorine-containing compound is generally from 0.01 ppm to 20%, particularly from 10 to 100 ppm.
  • the liquid containing the fluorine-containing compound may be adjusted to have pH of from 1 to 5 by adding an acid, for example, an inorganic acid such as hydrochloric acid, before the adsorption.
  • an acid for example, an inorganic acid such as hydrochloric acid
  • the fluorine-containing compound is adsorbed in the active carbon by contacting the liquid containing the fluorine-containing compound with the active carbon.
  • the temperature during the contact may be, for example, from 0 to 50° C. and the pressure may be, for example, from 0.1 to 10 atm, particularly 1 atm.
  • the contact time may be from 0.1 seconds to 100 hours, for example, from 1 second to 1 hour, particularly from 30 seconds to 1 minute.
  • the contact may be performed by either batch or flow process.
  • the adsorption rate of the fluorine-containing compound to the active carbon can be controlled by changing the pH of the liquid.
  • the pH of the liquid may be from 1.5 to 13.5, for example, from 2 to 13.
  • the active carbon that has adsorbed can be separated from the liquid containing the fluorine-containing compound by, for example, a filtration.
  • Desorption of the fluorine-containing compound can be performed by heating the active carbon, which has adsorbed the fluorine-containing compound, to a high temperature, for example, at least 150° C.
  • the temperature of the desorption may be, for example, at least 120° C., for example, from 120 to 350° C., particularly from 150 to 300° C.
  • the pressure may be from 0.1 to 10 atm, particularly 1 atm.
  • the heating time may be generally from 1 second to 10 hours, for example, from 1 minute to 2 hours.
  • Steam may be used as a heating medium for applying the heat.
  • the pressure of the steam may be generally at least 0.2 MPa, for example, from 0.2 to 15 MPa, particularly from 0.5 to 15 MPa.
  • the desorbed fluorine-containing compound can be recovered. Recovery of the desorbed fluorine-containing compound can be performed by collecting a steam containing the fluorine-containing compound.
  • the steam may be passed through water in a liquid phase, for example at a temperature of 5 to 70° C.
  • a vapor phase from the water in a liquid phase may be passed through an alkaline aqueous solution, for example, having a normality (N) of 0.01 to 10, particularly 0.1 to 1.0 and a temperature of 5 to 70° C.
  • FIG. 1 shows an apparatus to recover the fluorine-containing compound.
  • This apparatus has a collection tube 11 receiving an active carbon 1 (i.e. an active carbon tube), a pressure gauge 2 , a filter 3 , a backflow preventing valve 4 , a drain valve 5 , an uptake tube 6 receiving water, and an uptake tube 7 receiving an aqueous solution of 0.1N sodium hydroxide.
  • an active carbon 1 i.e. an active carbon tube
  • a pressure gauge 2 i.e. an active carbon tube
  • a filter 3 i.e. an active carbon tube
  • a backflow preventing valve 4 i.e. an active carbon tube
  • a drain valve 5 i.e. an uptake tube 6 receiving water
  • an uptake tube 7 receiving an aqueous solution of 0.1N sodium hydroxide.
  • the fluorine-containing compound When the steam containing the fluorine-containing compound flows through the uptake tube 6 , the fluorine-containing compound is dissolved in the water received in the uptake tube 6 , thereby collecting the fluorine-containing compound by the uptake tube 6 . Most of the fluorine-containing compound, which has been desorbed from the active carbon, is collected by the uptake tube 6 .
  • the fluorine-containing compound, which has not collected by the uptake tube 6 can be collected by the uptake tube 7 receiving an aqueous solution of from 0.1 to 1.0 N sodium hydroxide.
  • the collection tube 11 may be used also for adsorption of the fluorine-containing compound.
  • the active carbon can adsorb again the fluorine-containing compound by flowing a liquid containing the fluorine-containing compound through the collection tube.
  • the adsorption may be performed by either batch or flow process.
  • the batch process is generally preferable.
  • the liquid containing the fluorine-containing compound is charged into the adsorption tube and is mixed with stirring the liquid, preferably with stirring the liquid and the active carbon, at a temperature of 5 to 70° C., for example 10 to 40° C., for 0.5 minute to 60 minute, for example, for 1 minute to 10 minutes.
  • examples wherein the fluorine-containing compound in a liquid phase is adsorbed by an active carbon and examples wherein steam is applied to the active carbon which has adsorbed fluorine-containing compound (C 2 -C 8 fluorosurfactant) so that the adsorbed substances is desorbed from the active carbon.
  • each of six types of active carbons having different specific surface areas, which were prepared from the same material (coconut shell) was used.
  • DIAHOPE M006 F-400 manufactured by Calgon Mitsubishi Chemical Corporation
  • Shirasagi WH manufactured by Japan EnviroChemicals, Limited
  • each of active carbons (0.1 g) was charged and then 300 cc of aqueous solution containing 100 ppm of perfluorohexanoic acid (PFHA), which was adjusted to pH 2, was charged.
  • the bottle was shaken at a temperature of 25° C. for 24 hours by a shaking apparatus, to adsorb perfluorohexanoic acid (PFHA) by the active carbon. Then, the equilibrium amount of adsorption was calculated.
  • the concentrations of perfluorohexanoic acid (PFHA) in the raw water and the treated aqueous solution were compared, and the equilibrium adsorption amount of perfluorohexanoic acid (PFHA) per a unit weight of active carbon was determined.
  • Adsorption rate of perfluorohexanoic acid (PFHA) to each active carbon is shown in Table 1.
  • the adsorption rate (%) is given by: [[(Concentration of PFHA in initial raw water [ppm]) ⁇ (Concentration of PFHA in treated water after adsorption [ppm])] ⁇ (Amount of raw water [g])]/[(Amount of used active carbon [g]) ⁇ 1,000,000] ⁇ 100[%].
  • the adsorption rate (%) is represented by the equation (1) as follows:
  • [ adsorption ⁇ ⁇ rate ] ⁇ ⁇ [ ⁇ [ ( PFHA ⁇ ⁇ concentration in ⁇ ⁇ initial ⁇ ⁇ aqueous phase ⁇ [ ppm ] ) - ( PFHA ⁇ ⁇ concentration in ⁇ ⁇ treated ⁇ water ⁇ [ ppm ] ) ] ⁇ ( Amount ⁇ ⁇ of ⁇ ⁇ liquid ⁇ [ g ] ) [ ( Weight ⁇ ⁇ of active ⁇ ⁇ carbon ⁇ [ g ] ⁇ ) ⁇ 1000 , 000 ] ] ⁇ 100 ⁇ [ % ] ( 1 )
  • Example 2 The same operation as in Example 1 was repeated except for using an ion-impregnated active carbon.
  • the PFHA adsorption rates of the active carbons classified based on the impregnated ions are shown in Table 2.
  • Example 4 The same operation as in Example 1 was repeated except for using PFBA (perfluorobutanoic acid) which has 4 carbon atoms.
  • PFBA perfluorobutanoic acid
  • Table 4 The results of the PFBA adsorption rate of the active carbons, which have various specific surface areas, are shown in Table 4.
  • Example 2 The same operation as in Example 1 was repeated using PFHA and the relationship between the pH value and the adsorption rate was determined. Adjustment of pH was performed by adding hydrochloric acid, sulfuric acid or nitric acid.
  • the present invention provides an adsorption process in which high adsorption of the C 2 -C 6 fluorine-containing compound can be attained without any morphological change of the C 2 -C 6 fluorine-containing compound by the use of active carbon, and a desorption process in which active carbon and adsorbed substances can be recycled by desorbing the adsorbed substances from the active carbon.
  • the C 2 -C 6 fluorine-containing compound which are contained in industrial waste water and have possibility to cause environmental problems in the future, can be highly recovered from a liquid phase and recycled according to the present invention.

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  • Water Supply & Treatment (AREA)
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US12/676,292 2007-09-04 2008-09-03 Method of adsorbing and method of recovering fluorine-containing compound Active 2028-10-28 US8642804B2 (en)

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JP2007-228684 2007-08-04
JP2007228684 2007-09-04
PCT/JP2008/065829 WO2009031562A1 (fr) 2007-09-04 2008-09-03 Procédé d'adsorption et procédé de récupération de composé contenant du fluor

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Cited By (1)

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EP3646946A1 (fr) 2018-10-30 2020-05-06 Helmholtz-Zentrum für Umweltforschung GmbH-UFZ Procédé d'élimination des composés organiques polyfluorés de l'eau au moyen d'un absorbant et sa régénération

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EP2415716B1 (fr) * 2009-03-31 2017-03-08 Daikin Industries, Ltd. Procédé de collecte de l'acide fluorocarboxylique possédant une liaison éther
JP5799884B2 (ja) * 2012-04-13 2015-10-28 ダイキン工業株式会社 含フッ素化合物含有液の処理方法
JP5751685B1 (ja) * 2014-06-17 2015-07-22 独立行政法人国立高等専門学校機構 フッ素吸着材及びその製造方法
JP6123864B2 (ja) 2015-10-19 2017-05-10 ダイキン工業株式会社 炭素数２〜７の含フッ素有機酸および不純物を含む組成物の処理方法
AU2020256256A1 (en) 2019-04-03 2021-11-11 Calgon Carbon Corporation Perfluoroalkyl and polyfluoroalkyl sorbent materials and methods of use
EP4019124A4 (fr) * 2019-08-20 2023-10-04 Futamura Kagaku Kabushiki Kaisha Charbon actif adsorbant un composé per-et polyfluoroalkyle
WO2021112011A1 (fr) * 2019-12-05 2021-06-10 フタムラ化学株式会社 Échantillonneur de piégeage de composés per- et poly-fluoroalkyle

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